Trifluoroacetic acid → HCID 58388093, compound

HRID 2080210Notes

Reaction equation

HRID 2080210 reaction equation
[NH2:1][C:2]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].C1C=CC(CC(NCN[C@H](C(O)=O)CC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1.[CH2:51]([NH2:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CS(C)=O.O>[NH2:1][C:2]1[N:23]=[C:22]([NH:58][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 188218A-101HCID 231304982-aminochloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 58388093HCID 58388093, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 2-amino-6-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-101 (110 mg, 0.31 mmol) in dimethylsulfoxide (1 mL) were added benzylamine (1.8 mL, 16.5 mmol) and N,N-diisopropylethylamine (0.5 mL, 2.94 mmol), and the solution was stirred for 17 hours at 135° C. Water was added to the reaction mixture, which was then extracted with ethyl acetate, the organic layer was sequentially washed with water and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The obtained residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (23.4 mg, 0.0429 mmol, 14%) was obtained as a trifluoroacetic acid salt.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washthe organic layer was sequentially washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-97c968943c0d4a988082cfc0aff8108f
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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